Trans-1,2-Diaminocyclohexane

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trans-1,2-Diaminocyclohexane is an organic compound with the formula C₆H₁₀(NH₂)₂. This diamine is a building block for chiral ligands that are useful in asymmetric catalysis.

A mixture of cis-1,2-diaminocyclohexane and racemic-trans-1,2-diaminocyclohexane is produced by the hydrogenation of 1,2-diaminobenzene. The trans isomer can be resolved into the two enantiomers using tartaric acid as the resolving agent.^[1]

Ligands derived from chxn

Representative ligands prepared from this diamine are diaminocyclohexanetetraacetic acid (CyDTAH4), Trost ligand, and the salen analogue used in the Jacobsen epoxidation.

References

^ Jay F. Larrow and Eric N. Jacobsen (2004). "(R,R)-N,N'-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst". Organic Syntheses; Collected Volumes, vol. 10, p. 96.

[1] Jay F. Larrow and Eric N. Jacobsen (2004). "(R,R)-N,N'-Bis(3,5-Di-tert-Butylsalicylidene)-1,2-Cyclohexanediamino Manganese(III) Chloride, A Highly Enantioselective Epoxidation Catalyst". Organic Syntheses; Collected Volumes, vol. 10, p. 96.

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